There are conventionally known various methods of and producing an ester compound which is the organic compound with an added ester group, by using an organic compound having an unsaturated bond and a formic acid compound as raw materials, without substantially using carbon monoxide.
For example, Non-Patent Literature 1 discloses a method for producing methyl propionate, which is a product of addition of methyl formate to ethylene, by reacting ethylene and methyl formate for 18 hours under the temperature conditions of 190° C., while using a ruthenium compound having a phosphine ligand as a catalyst. According to this disclosed method, methyl propionate is produced in an amount of 286 molar equivalents with respect to the ruthenium compound.
Non-Patent Literature 2 discloses a method for producing methyl propionate, which is a product of addition of methyl formate to ethylene, by reacting ethylene and methyl formate for 2 hours under the temperature conditions of 160° C. in DMF solvent, while using a ruthenium compound having a carbonyl ligand and a chlorine ligand as a catalyst. According to this disclosed method, methyl propionate is produced in an amount of 345 molar equivalents with respect to the ruthenium compound.
Patent Literature 1 discloses a method for producing methyl propionate by reacting ethylene and methyl formate to react for one hour under the temperature conditions of 190° C. in DMF solvent and in the presence of a catalyst system composed of a ruthenium compound having a ligand selected from the group consisting of a carbonyl ligand, a chlorine ligand and an amine ligand, and a quaternary ammonium iodide. According to this disclosed method, methyl propionate is produced in an amount of 1530 molar equivalents with respect to the ruthenium compound.
Non-Patent Literature 3 discloses a method for producing a compound which is norbornene with an added ester group, by reacting norbornene and methyl formate for 15 hours under the temperature conditions of 170° C. in toluene, while using a combination of a ruthenium carbonyl cluster compound and a tertiary phosphine compound as a catalyst. According to this disclosed method, the compound which is norbornene with an added ester group is obtained at a yield of 22% in terms of methyl formate. Furthermore, when benzyl formate is used instead of methyl formate, the corresponding ester compound is obtained at a yield of 77%.
Non-Patent Literature 4 discloses a method of reacting 1-hexene and a formic acid compound having a pyridine group for 4 hours under the temperature conditions of 135° C. in DMF solvent, while using a ruthenium carbonyl cluster compound as a catalyst, and thereby producing a corresponding ester compound. According to this disclosed method, the ester compound is obtained at a yield of 98% in terms of the formic acid compound.
The various methods described above are highly useful as methods for producing a desired ester compound from an organic compound having an unsaturated bond, even among a variety of methods for producing ester compounds, since the use of toxic raw materials such as carbon monoxide is unnecessary, and the reaction proceeds at a relatively low pressure.